San Gimignanello Vacation Villa Rentals
Results 221 - 240 of 496
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Description
Property Summary
Nestled among the rolling hills of the Tuscan countryside, "Casino di Lecceto" is a large, rustic cottage offering an authentic and secluded retreat in Italy, just 8 km from the historic centre of Siena. Set at 400 metres above sea level and spread across 3 storeys, this detached property sits majestically on top of a hill, surrounded by trees and embraced by the natural beauty of the surrounding woodland. As a holiday rental of remarkable character and charm, the cottage accommodates guests seeking privacy and immersion in nature without sacrificing comfort. The property benefits from a generous private estate of 2 hectares, fully fenced and maintained in its natural state, encompassing a wildlife garden, a natural garden, a meadow, and a courtyard. A private swimming pool measuring 10 x 5 metres is available for guests during its seasonal opening period, from 24 April to 4 October, and is maintained by the owner's gardener. The yard surrounding the property provides ample space to enjoy the tranquil outdoor setting, while parking is conveniently available directly on the premises. Internet Wi-Fi connectivity ensures that guests can remain connected throughout their stay, even in this wonderfully remote location.
Outdoors
The outdoor spaces of "Casino di Lecceto" are a true highlight of the property, offering a harmonious blend of cultivated and natural environments across an expansive 2-hectare estate. The private grounds include a wildlife garden, a natural garden, a meadow, and a courtyard, all maintained in a manner that respects and celebrates the surrounding landscape. The swimming pool, measuring 10 x 5 metres, is available seasonally from 24 April to 4 October and is regularly serviced by the owner's gardener to ensure it remains in excellent condition throughout the season. A terrace provides an ideal setting for outdoor relaxation and dining, furnished with garden furniture to allow guests to enjoy meals and leisure time in the open air. A barbecue is also available, perfect for alfresco dining during warm Tuscan evenings. Walking paths begin just 1 km from the property, inviting guests to explore the surrounding countryside and woodland at their own pace.
Other Information
"Casino di Lecceto" is a detached, 3-storey rustic cottage situated in a secluded position, and guests should be aware that part of the house is closed and unoccupied during their stay. Access to the property is via a 400-metre unmade road that is very bumpy, and a 4x4 vehicle is strongly recommended, particularly during the winter months. Please be advised that the tap water at the property does not meet drinking water quality standards, and guests are encouraged to use bottled water for drinking purposes. Baby equipment is included in the rental at no additional charge, making the property a practical choice for families with young children. Groups of teenagers are accommodated on request only and must be arranged in advance. The property is surrounded by trees and positioned 100 metres from the edge of the forest, offering a genuinely immersive natural experience in the Tuscan hills.
Distances and Attractions
"Casino di Lecceto" enjoys a privileged position that provides convenient access to a wealth of destinations and services. Essential amenities are within easy reach, with a grocery store located 1 km away, a supermarket 5 km away, and a restaurant just 2 km from the property. A bus stop is situated 2 km away, while the railway station "Siena" is 8 km from the cottage. The vibrant city of Siena, with its world-renowned historic centre, is just 8 km away, while Florence lies approximately 80 km from the property. The charming medieval town of San Gimignano is 50 km away, and the beautifully preserved walled village of Monteriggioni can be reached in just 14 km. For those interested in history and culture, a former hermitage featuring 15th-century frescoes is located just 1 km from the property. The remarkable ruined abbey of San Galgano is 28 km away, and the ancient Etruscan city of Volterra is 50 km from the cottage. Nature and wellness enthusiasts will appreciate the proximity of the thermal baths at "Rapolano Terme," situated 37 km away. An 18-hole golf course is available 16 km from the property. For those wishing to visit the coast, the sandy beach of "Follonica" is 80 km away, as is the sea. Casino di Lecceto
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Description
Property Summary
Nestled in the rolling Tuscan countryside of Siena, Italy, the charming detached house "L'Oliviera" offers a truly peaceful and sun-drenched retreat for those seeking an authentic holiday rental experience. Positioned in a quiet, elevated setting just 5 km from the historic centre of Siena, this beautiful property is surrounded by trees, open fields, and sits only 100 metres from the edge of a forest, creating a natural and serene atmosphere. The house benefits from complimentary Wi-Fi throughout, allowing guests to stay connected while enjoying the tranquillity of the Tuscan landscape. Private parking is conveniently available directly at the property, ensuring effortless arrivals and departures for those exploring the surrounding region by car.
Outdoors
The outdoor spaces of "L'Oliviera" are a true highlight of the property, offering guests a private and immersive connection with the natural Tuscan environment. The grounds feature a well-maintained lawn alongside a wildlife garden, thoughtfully designed to blend harmoniously with the surrounding countryside and its native flora and fauna. The property is enveloped by trees and open fields, providing a sense of seclusion and privacy that makes it an ideal setting for relaxing outdoors, breathing in the fresh country air, and enjoying the unspoiled beauty of the Sienese hills.
Other Information
Guests should be aware that heating at "L'Oliviera" is available and billed on-site, applicable during the period from 10 April to 31 October. Baby equipment is provided and included at no additional charge, making the property a practical and welcoming choice for families travelling with young children. The owner resides on the same property, ensuring a reassuring presence and the opportunity for personalised local assistance throughout the stay. Guests should also be aware that the owner keeps a dog on the premises. As the property is situated in a rural setting, the use of a car is strongly recommended in order to fully enjoy the surrounding area and access nearby services with ease.
Distances and Attractions
"L'Oliviera" enjoys a convenient location with easy access to a wide range of everyday amenities and cultural landmarks. A grocery store is located just 3 km away, while a shopping centre can be reached within 4 km, and a restaurant is a short 2 km drive from the property. Public transport is readily accessible, with a bus stop situated only 100 metres from the house, and the railway station "Siena" reachable within 6 km. For those wishing to explore the wider Tuscan region, the thermal baths of "Rapolano Terme" are approximately 35 km away, offering a wonderful opportunity for relaxation and wellness. The medieval village of Monteriggioni lies just 16 km from the property, while the iconic hilltop town of San Gimignano is 36 km away. The breathtaking landscape of the Crete Senesi can be explored within 30 km, and the celebrated wine town of Montalcino is situated 45 km from the house. The Renaissance gem of Pienza is approximately 50 km away, and Montepulciano, renowned for its Vino Nobile, can be reached within 65 km, making "L'Oliviera" an exceptional base from which to discover the very best of Tuscany. L'Oliviera
La Dimora del Chianti Dimora: Stunning Tuscan Vill
Stunning private vacation home with A/C, private pool, WIFI and TV
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Description
La Dimora del Chianti Dimora: Stunning Tuscan Vill is located 5 km (3 mi) from Rietine, Italy and only 27 km (17 mi) from Siena in the tourist area "Siena And Surroundings". La Dimora del Chianti Dimora: Stunning Tuscan Vill is a lovely property (200 sq m) with private pool, WiFi internet and air conditioning. The property can accommodate up to eight guests comfortably in four bedrooms with five bathrooms.
What to Expect
After arriving you’ll find a nice clean well-maintained property with views of the hills ideal for a relaxing vacation in Tuscany. Regardless of how you spend your days - visiting museums, sightseeing, shopping or just driving in the countryside, when you arrive home you can unwind with your family and friends at the pool for a perfect ending to another day in Tuscany. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. If you prefer to dine 'al fresco', there is a fully furnished garden where you can enjoy the weather while dining outdoors.
Visit the Area
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Siena 27 km (17 mi), Greve In Chianti 33 km (21 mi), Arezzo 52 km (32 mi), San Gimignano 54 km (33 mi) and Montalcino 62 km (38 mi).
Some other major tourist destinations you should consider visiting are: Florence 65 km (41 mi), Viareggio 159 km (99 mi), Forte Dei Marmi 167 km (103 mi), Rome 240 km (149 mi), Venice 316 km (196 mi) and Milan 359 km (223 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 19 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 78 km (49 mi), Pisa (psa) 124 km (77 mi), Bologna (blq) 165 km (102 mi), Roma Ciampino (cia) 249 km (155 mi) and Roma Fiumicino (fco) 261 km (162 mi).
La Dimora del Chianti Dimora: Stunning Tuscan Vill
Book now and save 10%. Offer valid until 20 April 2026 and for a minimum stay of 5 nights.
Villa del Mangia, 5Panoramic Pool and Chef Service
Superb private holiday rental with WIFI, A/C, private pool, terrace and panoramic view
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Description
Villa del Mangia is a villa located just a few kilometers from Siena.
The villa consists of a main building spread over two floors and an external annex, a former stone barn, which serves as the guesthouse. The total area of the property is 400 sqm. The entire complex was fully renovated in 2024, with incredible attention to detail and the use of high-quality materials, skillfully combining the charm of Tuscan tradition with modern comforts, furnishings, and top-tier materials, offering a luxurious and sophisticated environment. The villa, meticulously curated in every detail, reflects the refined taste of the owner and an emphasis on rare, high-quality materials.
The outdoor spaces have been designed with great care, creating a harmonious connection between the villa and the surrounding natural environment. The garden features lush terraced areas, olive trees, and spacious open areas, ideal for hosting large families or groups of friends seeking a relaxing and convivial vacation.
The interiors, enhanced by marbles that provide luminosity and contemporary design, are equipped with a floor heating and cooling system to ensure maximum comfort. At the same time, original elements such as the ceilings and exposed beams preserve the villa's historic charm, offering a perfect balance between the old and the new.
The annexed barn is equally welcoming, with a breathtaking view of Siena: every window in this building frames a picture-perfect scene.
The spacious indoor and outdoor areas provide the opportunity to enjoy moments together without sacrificing tranquility or the possibility of retreating to more intimate spaces. Ideal for large families or groups wanting to spend a pleasant vacation together while maintaining privacy, this villa allows you to fully enjoy the Sienese countryside, while being just a short drive from some of Tuscany's most famous destinations, such as Siena, San Gimignano, and Florence. Villa del Mangia, 5Panoramic Pool and Chef Service
Book your vacation for the period from 01 June 2026 to 26 June 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 01 July 2026 to 31 July 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 09 September 2026 to 19 September 2026 and save 10% (minimum 3 nights).
Book your vacation for the period from 13 October 2026 to 31 October 2026 and save 10% (minimum 3 nights).
Le Loggine del Pignatello Apartment, Siena City
Comfortable apartment with WIFI and TV
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Description
In the heart of Siena’s historic center, a two-level apartment with access from a charming internal courtyard that offers an authentic and peaceful atmosphere.
Stay in this accommodation to explore the city of Siena and nearby attractions. A must-see is Piazza del Campo, the heart of Siena and one of the most beautiful medieval squares in Europe. This is where the famous Palio di Siena takes place (July 2nd and August 16th). Climbing the Torre del Mangia (about 400 steps) rewards you with a spectacular view over the city’s rooftops and the Tuscan countryside. The Siena Cathedral is one of the most fascinating in Italy, featuring unique inlaid floors and works by Michelangelo, Donatello, and Pisano.
Nearby, you can visit San Gimignano with its medieval towers, the Val d’Orcia with its iconic landscapes, Monteriggioni, a fortified village, and Montalcino, famous for its Brunello wine cellars.
The cities of Florence and Arezzo are also easily reachable.
Parking available on request at an extra cost of €35 per day.
Distance to the bus stop: 20 meters from the front door, with a direct connection to the station escalator in less than 5 minutes. Le Loggine del Pignatello Apartment, Siena City
Villetta di Cortona
Private House with A/C, private pool, WIFI, TV, patio, pets allowed, panoramic view
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Description
Villetta Di Cortona is a nice holiday rental (90 sq m) with WiFi internet, private pool and air conditioning. The property can accommodate up to four people comfortably in two bedrooms with two bathrooms. Villetta Di Cortona is located 12 km (7 mi) from Cortona, Italy and only 22 km (14 mi) from Montepulciano.
The Experience
After arriving you’ll find a nice clean well-maintained property perfect for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of visiting museums. Outdoors you will also find a patio and barbecue grill.
Places Nearby
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montepulciano 22 km (14 mi), Perugia 49 km (30 mi), Arezzo 49 km (30 mi), Montalcino 57 km (35 mi) and Siena 65 km (40 mi).
Some other major tourist destinations you should consider visiting are: Florence 121 km (75 mi), Viareggio 207 km (129 mi), Forte Dei Marmi 214 km (133 mi), Rome 202 km (126 mi), Venice 364 km (226 mi) and Milan 407 km (253 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villetta Di Cortona. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 16:00 - 19:00
Check-Out Time: 06:00 - 09:00
Pool Open: 15 April - 15 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 128 km (79 mi), Pisa (psa) 188 km (117 mi), Roma Ciampino (cia) 212 km (131 mi), Bologna (blq) 212 km (132 mi) and Roma Fiumicino (fco) 224 km (139 mi).
The garden is fully enclosed.
Up to 3 dogs are accepted. Villino Cortona
Book your vacation for the period from 04 April 2026 to 16 May 2026 and save 25% (minimum 3 nights).
Book your vacation for the period from 26 September 2026 to 28 November 2026 and save 25% (minimum 3 nights).
Villa Margherita
Unique independent accommodation with WIFI, private pool, TV, patio, pets allowed and panoramic view
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Description
Charming independent villa with private swimming-pool situated in panoramic location, on the hills around the beautiful medieval town of Cortona, approx. 750 m above sea level. This property is surrounded by beautiful woods and offers tastefully furnished interiors and a cosy atmosphere. The location is ideal to enjoy the peace of the Tuscan landscape and at the same time to visit the most important historical cities of the area.
The access to the property is via an unpaved but well-maintained road.
Distances: the small village of Portole with food shops 6 km away, Cortona with al kinds of shops 13 km, Città di Castello and Arezzo approx. 40 km. Lake Trasimeno is about 30 km away.
At guests’ disposal: furnished garden, beautiful irregular-shaped swimming-pool (ca. 7 x 14 m – maximum depth 2,4 m), veranda equipped with tables and chairs for “al fresco” dining, barbecue. Use of a washing-machine and ironing facilities. Parking with the grounds.
Extra Services: Baby bed available on request. Upon request chef service available for nice Tuscan dinners.
Please carefully check if there are any extra costs to be paid on site! Villa Margherita
Book 14 days or less before the arrival date and receive a 20 % discount off the published rental rates.
This Offer is valid only for stays of 7 nights minimum and can not be combined with any other special offers.
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Description
Conveniently located 3 km (2 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 27 km (16 mi) from Arezzo. Holiday rental Villa Gelsi is a nice stone building (230 sq m) that includes private pool, air conditioning and WiFi internet. The property can sleep up to 15 people comfortably in nine bedrooms with eight bathrooms.
What to Expect
When you arrive you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property perfect for a relaxing vacation in Tuscany. After a busy day of sightseeing, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to unwind at the end the day.
Visit the Area
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 27 km (16 mi), Montepulciano 31 km (19 mi), Perugia 51 km (32 mi), Montalcino 65 km (40 mi) and Assisi 73 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 118 km (73 mi), Viareggio 204 km (127 mi), Forte Dei Marmi 212 km (131 mi), Rome 211 km (131 mi), Milan 405 km (251 mi) and Naples 402 km (249 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 123 km (76 mi), Pisa (psa) 186 km (115 mi), Bologna (blq) 210 km (130 mi), Roma Ciampino (cia) 220 km (136 mi) and Roma Fiumicino (fco) 232 km (144 mi).
Villa Gelsi
Villa i Cocciai
Wonderful private accommodation with private pool, A/C, WIFI, TV, terrace and panoramic view
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Description
Villa i Cocciai is located in Cortona, Italy and only 29 km (18 mi) from Arezzo in the tourist area "Cortona And Surroundings". Vacation rental Villa i Cocciai is a beautiful stone building (185 sq m) that includes air conditioning, private pool and WiFi internet. The property can sleep up to eight guests comfortably in four bedrooms with four bathrooms.
What to Expect
When you arrive at Villa i Cocciai you’ll find a lovely clean well-maintained property with views of the hills ideal for a relaxing vacation in Tuscany. After a hectic day of visiting museums, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. If you prefer to dine 'al fresco', there is a fully furnished terrace where you can enjoy the weather while dining outdoors.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 29 km (18 mi), Montepulciano 30 km (18 mi), Perugia 52 km (32 mi), Montalcino 64 km (40 mi) and Gubbio 69 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 128 km (79 mi), Viareggio 214 km (133 mi), Forte Dei Marmi 222 km (138 mi), Rome 210 km (130 mi), Venice 371 km (230 mi) and Milan 414 km (257 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 126 km (78 mi), Pisa (psa) 187 km (116 mi), Bologna (blq) 211 km (131 mi), Roma Ciampino (cia) 218 km (135 mi) and Roma Fiumicino (fco) 231 km (143 mi).
More Services
Cooking Lessons - Discover from a local chef the techniques required to master Tuscan cuisine. The owner can organize to have a chef come to the property for a cooking lesson for any number of people in your group. It's a fun way to spend time with friends and family while discovering the secrets vital to prepare sumptuous Tuscan meals when you return home. For more details and the extra cost, please contact us.
Tours - Custom tours can be organized by the owner for your group. For more details about the tours offered, speak to the owner when you arrive or ask prior to booking. The cost will vary depending in the specific tour and number of people.
Baby Sitting - A babysitter can be scheduled at Villa i Cocciai. If you're traveling with kids and would like some alone time, talk to the owner directly about this option after arriving.
Villa i Cocciai
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Description
Holiday rental Casa Cristina is a nice property that includes WiFi internet and private pool. The property can accommodate up to four guests comfortably. Conveniently located 7 km (4 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 34 km (21 mi) from Arezzo.
Casa Cristina is the annex of a larger villa where the owners live, but at the same time it's totally independent and exclusively for the use of guests with private garden and pool only available to occupants of the cottage.
The Experience
Upon arrival you will be welcomed by the owner or manager where you’ll find a nice clean well-maintained property with views of the hills and the mountains perfect for a peaceful holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a hectic day of sightseeing. Dining with friends and family is a big part of the Tuscan culture. Take advantage of the well-equipped kitchen to prepare meals using local produce while on your vacation. The kitchen includes coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to four people. Dine 'al fresco' like a real Tuscan, the fully furnished terrace is the ideal setting to enjoy food, family and the nice Tuscan weather.
Places Nearby
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 34 km (21 mi), Montepulciano 37 km (23 mi), Perugia 59 km (37 mi), Montalcino 71 km (44 mi) and Gubbio 75 km (47 mi).
Some other major tourist destinations you should consider visiting are: Florence 128 km (80 mi), Viareggio 222 km (138 mi), Forte Dei Marmi 229 km (142 mi), Rome 217 km (135 mi), Venice 378 km (235 mi) and Milan 421 km (262 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 142 km (88 mi), Pisa (psa) 203 km (126 mi), Bologna (blq) 223 km (138 mi), Roma Ciampino (cia) 226 km (140 mi) and Roma Fiumicino (fco) 238 km (148 mi).
Additional Services
Cooking Lessons - Discover from a local chef the techniques needed to master Tuscan cuisine. The owner can arrange to have a chef come to the property for a cooking lesson for any number of people in your group. It's a pleasant way to spend time with friends and family while learning the secrets required to prepare delicious Tuscan meals when you return home. For more details and the supplemental cost, please contact us.
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a sumptuous meal using local produce? The chef will arrange the meal based on your preferences and dietary requirements. The chef will offer advice for the various courses and the wine. Inquire for more details and the additional costs.
Tours - Custom tours can be scheduled by the owner for your group. For more details about the tours available, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be arranged. Speak to the owner directly about this service after arriving.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
Casa Cristina
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Description
Conveniently located 9 km (5 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 36 km (22 mi) from Arezzo. La Montana is a lovely stone building (145 sq m) with private pool, air conditioning and WiFi internet. The property can sleep up to six guests comfortably in three bedrooms with three bathrooms.
Your Experience
When you arrive you’ll find a nice clean well-maintained property with views of the mountains and the hills ideal for a relaxing vacation in Tuscany. Regardless of how you spend your days - shopping, visiting museums, sightseeing or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. For your pleasure, on the grounds there is a playground and barbecue grill.
Visit the Area
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 36 km (22 mi), Montepulciano 38 km (24 mi), Perugia 59 km (37 mi), Gubbio 67 km (41 mi) and Montalcino 73 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 118 km (73 mi), Viareggio 204 km (127 mi), Forte Dei Marmi 211 km (131 mi), Rome 218 km (136 mi), Milan 404 km (251 mi) and Naples 409 km (254 mi).
Additional Information
Pool Open: 26 April - 1 November (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 123 km (76 mi), Pisa (psa) 185 km (115 mi), Bologna (blq) 209 km (130 mi), Roma Ciampino (cia) 227 km (141 mi) and Roma Fiumicino (fco) 240 km (149 mi).
More Services
Tours - Custom tours can be organized by the owner for your group. For more details about the tours offered, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the exact tour and number of people.
La Montana
Villa Il Sasso
Beautiful independent vacation home with private pool, A/C, WIFI, TV, terrace and panoramic view
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Description
Villa Il Sasso is located in Cortona, Italy and only 29 km (18 mi) from Montepulciano in the tourist area "Cortona And Surroundings". Vacation rental Villa Il Sasso is a beautiful stone building (450 sq m) that includes air conditioning, private pool and WiFi internet. The property can sleep up to 13 people comfortably in seven bedrooms with five bathrooms.
Your Experience
Upon arrival at Villa Il Sasso you’ll find a lovely clean well-maintained property with views of the hills and the city ideal for a splendid holiday in Tuscany. For your pleasure you will find a private pool where you can unwind while enjoying a nice cold beverage after a busy day of sightseeing. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 13 people. If you prefer to dine 'al fresco', there is a fully furnished terrace where you can enjoy the weather while dining outdoors.
Places Nearby
Most people enjoy visiting close-by cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montepulciano 29 km (18 mi), Arezzo 30 km (18 mi), Perugia 51 km (32 mi), Montalcino 63 km (39 mi) and Gubbio 69 km (43 mi).
Some other major tourist destinations you should consider visiting are: Florence 127 km (79 mi), Viareggio 214 km (133 mi), Forte Dei Marmi 221 km (137 mi), Rome 209 km (130 mi), Venice 370 km (230 mi) and Milan 414 km (257 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 30 April - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 135 km (84 mi), Pisa (psa) 195 km (121 mi), Roma Ciampino (cia) 218 km (136 mi), Bologna (blq) 219 km (136 mi) and Roma Fiumicino (fco) 231 km (143 mi).
More Services
Tours - The owner can schedule custom tours for your group. To learn about the tours available, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the specific tour and number of people.
Baby Sitting - If you're traveling with children and would like an evening alone, a babysitter can be organized. Speak to the owner directly about this service when you arrive.
Villa Il Sasso
Tenuta Pomona
Superb independent villa rental with WIFI, A/C, private pool, TV, patio and panoramic view
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Description
Property Tenuta Pomona is a nice stone building (189 sq m) that includes air conditioning, private pool and WiFi internet. The property can sleep up to eight guests comfortably in four bedrooms with three bathrooms. Conveniently located 9 km (5 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 28 km (18 mi) from Arezzo.
The accommodation consists of the main villa in stone, which can comfortably accommodate up to 6 people and a dependance, where 2 additional guests can stay.
What to Expect
After arriving you will be welcomed by the owner or manager where you’ll find a lovely clean well-maintained property with views of the city and the hills ideal for a peaceful holiday in Tuscany. Regardless of how you spend your days - sightseeing, shopping, visiting museums or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Outdoors you will also find a barbecue grill and patio. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
Places Nearby
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 28 km (18 mi), Montepulciano 33 km (20 mi), Perugia 55 km (34 mi), Montalcino 67 km (42 mi) and Assisi 72 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 118 km (74 mi), Viareggio 205 km (127 mi), Forte Dei Marmi 212 km (132 mi), Rome 213 km (132 mi), Venice 362 km (225 mi) and Milan 405 km (251 mi).
Additional Information
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 May - 30 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 126 km (78 mi), Pisa (psa) 186 km (116 mi), Bologna (blq) 210 km (131 mi), Roma Ciampino (cia) 220 km (137 mi) and Roma Fiumicino (fco) 232 km (144 mi).
More Services
Tours - The owner can organize custom tours for your group. To learn about the tours available, speak to the owner after arriving or inquire prior to booking. The cost will vary depending in the specific tour and number of people.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you check-in that is possible at Tenuta Pomona. Ask for more details, including the extra cost and how to arrange this service.
Baby Sitting - A babysitter can be organized at Tenuta Pomona. If you're traveling with kids and would like some alone time, talk to the owner directly about this option when you arrive.
Tenuta Pomona
La Montanina
Fabulous private vacation rental with private pool, A/C, WIFI, TV, veranda and panoramic view
- 4
- 2
- 2
Description
La Montanina is a lovely stone building (75 sq m) with private pool, air conditioning and WiFi internet. The property can sleep up to four guests comfortably in two bedrooms with two bathrooms. Conveniently located 9 km (5 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 36 km (22 mi) from Arezzo.
Your Experience
Upon arrival at La Montanina you’ll find a beautiful clean well-maintained property with views of the lake and the hills ideal for a relaxing holiday in Tuscany. Regardless of how you spend your days - visiting museums, shopping, sightseeing or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Also available outside are a barbecue grill and playground.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 36 km (22 mi), Montepulciano 38 km (24 mi), Perugia 59 km (37 mi), Gubbio 67 km (41 mi) and Montalcino 73 km (45 mi).
Some other major tourist destinations you should consider visiting are: Florence 118 km (73 mi), Viareggio 204 km (127 mi), Forte Dei Marmi 211 km (131 mi), Rome 218 km (136 mi), Milan 404 km (251 mi) and Naples 409 km (254 mi).
Additional Information
Pool Open: 26 April - 1 November (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 123 km (76 mi), Pisa (psa) 185 km (115 mi), Bologna (blq) 209 km (130 mi), Roma Ciampino (cia) 227 km (141 mi) and Roma Fiumicino (fco) 240 km (149 mi).
More Services
Tours - The owner can arrange custom tours for your group. To learn about the tours available, speak to the owner when you arrive or ask prior to booking. The cost will vary depending in the exact tour and number of people.
La Montanina
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- 4
- 2
Description
Villa Elena is located 15 km (9 mi) from Cortona, Italy and only 19 km (12 mi) from Montepulciano. Vacation rental Villa Elena is a nice property (120 sq m) that includes WiFi internet, air conditioning and private pool. The property can accommodate up to seven people comfortably in four bedrooms with two bathrooms.
What to Expect
When you arrive you’ll find a nice clean well-maintained property with views of the hills perfect for a relaxing holiday in Tuscany. Regardless of how you spend your days - visiting museums, sightseeing, shopping or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. Also available outdoors are a barbecue grill and patio. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to seven people. If you prefer to dine 'al fresco', there is a fully furnished veranda where you can enjoy the weather while dining outdoors.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montepulciano 19 km (12 mi), Perugia 49 km (30 mi), Arezzo 53 km (33 mi), Montalcino 55 km (34 mi) and Assisi 70 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 125 km (78 mi), Viareggio 212 km (132 mi), Forte Dei Marmi 219 km (136 mi), Rome 207 km (129 mi), Milan 412 km (256 mi) and Naples 398 km (247 mi).
Additional Information
Pool Open: 1 April - 31 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 130 km (81 mi), Pisa (psa) 193 km (120 mi), Roma Ciampino (cia) 216 km (134 mi), Bologna (blq) 217 km (135 mi) and Roma Fiumicino (fco) 229 km (142 mi).
More Services
Tours - The owner can organize custom tours for your group. To learn about the tours available, speak to the owner upon arrival or ask prior to booking. The cost will vary depending in the specific tour and number of people.
Villa Elena
Book your vacation for the period from 04 April 2026 to 30 May 2026 and save 10% (minimum 7 nights). Offer valid until 30 May 2026.
Casa i Pini
Fabulous private villa rental with private pool, A/C, WIFI, TV, pets allowed and panoramic view
- 8
- 4
- 4
Description
Casa i Pini is located 7 km (4 mi) from Cortona, Italy and only 29 km (18 mi) from Montepulciano in the tourist area "Cortona And Surroundings". Casa i Pini is a beautiful stone building (180 sq m) with private pool, air conditioning and WiFi internet. The property can accommodate up to eight people comfortably in four bedrooms with four bathrooms.
The accommodation consists of a main building and an annex and can accommodate up to 8 people: 6 in the main house (180 sq m) and 2 in the annex (50 square meters).
What to Expect
Upon arrival at Casa i Pini you’ll find a nice clean well-maintained property with views of the hills ideal for a peaceful vacation in Tuscany. After a busy day of shopping, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to unwind at the end the day. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster and refrigerator, as well as, plenty of tableware and cutlery for up to eight people. If you prefer to dine 'al fresco', there is a fully furnished garden where you can enjoy the weather while dining outdoors.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montepulciano 29 km (18 mi), Arezzo 32 km (20 mi), Perugia 54 km (34 mi), Montalcino 58 km (36 mi) and Siena 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 122 km (76 mi), Viareggio 209 km (130 mi), Forte Dei Marmi 216 km (134 mi), Rome 204 km (127 mi), Venice 361 km (224 mi) and Milan 406 km (252 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Casa i Pini. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 April - 15 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 127 km (79 mi), Pisa (psa) 190 km (118 mi), Roma Ciampino (cia) 213 km (132 mi), Bologna (blq) 214 km (133 mi) and Roma Fiumicino (fco) 225 km (140 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be scheduled at the property. It's a pleasant way to spend time with friends and family while learning the techniques vital to master Tuscan cuisine. For more details and the additional cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will arrange the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Ask for more details and the supplemental costs.
Tours - The owner can organize custom tours for your group. To learn about the tours available, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the individual tour and number of people.
Baby Sitting - A babysitter can be scheduled at Casa i Pini. If you're traveling with kids and would like some alone time, speak to the owner directly about this option upon arrival.
Casa i Pini
Orangerie degli Ulivi
Unique private villa with A/C, WIFI, private pool, terrace, pets allowed, panoramic view
- 4
- 2
- 1
Description
Conveniently located in Cortona, Italy in the tourist area "Cortona And Surroundings" and only 29 km (18 mi) from Arezzo. Vacation rental Orangerie Degli Ulivi is a lovely stone building (60 sq m) that includes air conditioning, private pool and WiFi internet. The property can accommodate up to four people comfortably in two bedrooms with one bathroom.
The owner lives on the property, but both the pool and the garden are for the guests' exclusive use; only the parking space is to be shared.
What to Expect
When you arrive you will be welcomed by the owner or manager where you’ll find a lovely clean well-maintained property with views of the hills perfect for a splendid vacation in Tuscany. For your enjoyment you will find a private pool where you can relax while enjoying a nice cold beverage after a hectic day of visiting museums. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to four people. If you prefer to dine 'al fresco', there is a fully furnished terrace where you can enjoy the weather while dining outdoors.
Visit the Area
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 29 km (18 mi), Montepulciano 31 km (19 mi), Perugia 52 km (33 mi), Montalcino 66 km (41 mi) and Gubbio 71 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 119 km (74 mi), Viareggio 206 km (128 mi), Forte Dei Marmi 213 km (132 mi), Rome 211 km (131 mi), Venice 359 km (223 mi) and Milan 404 km (251 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Orangerie Degli Ulivi. If you have a large dog or multiple pets, please ask for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 1 April - 31 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 125 km (77 mi), Pisa (psa) 187 km (116 mi), Bologna (blq) 211 km (131 mi), Roma Ciampino (cia) 220 km (137 mi) and Roma Fiumicino (fco) 233 km (145 mi).
Additional Services
Cooking Lessons - If you're interested in discovering more about Tuscan cooking, inquire about the cooking lessons that can be scheduled at the property. It's a pleasant way to spend time with friends and family while learning the techniques required to master Tuscan cuisine. For more details and the extra cost, please contact us.
Professional Chef - Are you looking for a real treat during your holiday? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will organize the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Ask for more details and the additional costs.
Tours - The owner can arrange custom tours for your group. To learn about the tours available, speak to the owner upon arrival or inquire prior to booking. The cost will vary depending in the specific tour and number of people.
Pre-Stocked Fridge - If you'd like to have the fridge and pantry stocked before you arrive that is possible at Orangerie Degli Ulivi. Ask for more details, including the extra cost and how to schedule this service.
Baby Sitting - A babysitter can be arranged at Orangerie Degli Ulivi. If you're traveling with kids and would like some alone time, talk to the owner directly about this option upon arrival.
Owner Assistance - Since the owner lives nearby, he is always available to offer advice and suggestions during your visit. In case you need assistance, it's nice to have someone available to help. In any case, the owner will always respect your privacy.
Orangerie Degli Ulivi
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- 3
- 4
Description
Holiday home Villa Luana is a beautiful stone building (150 sq m) that includes air conditioning, private pool and WiFi internet. The property can sleep up to eight guests comfortably in three bedrooms with four bathrooms. Conveniently located 3 km (2 mi) from Cortona, Italy in the tourist area "Cortona And Surroundings" and only 29 km (18 mi) from Arezzo.
Your Experience
When you arrive you’ll find a nice clean well-maintained property with views of the hills and the city ideal for a splendid holiday in Tuscany. After a hectic day of visiting museums, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to unwind at the end the day.
What's Nearby?
Most people enjoy visiting close-by cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 29 km (18 mi), Montepulciano 32 km (20 mi), Perugia 54 km (33 mi), Montalcino 67 km (42 mi) and Gubbio 72 km (44 mi).
Some other major tourist destinations you should consider visiting are: Florence 120 km (75 mi), Viareggio 204 km (127 mi), Forte Dei Marmi 214 km (133 mi), Rome 212 km (132 mi), Venice 360 km (224 mi) and Milan 407 km (253 mi).
Additional Information
Pool Open: 15 April - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 126 km (78 mi), Pisa (psa) 188 km (117 mi), Bologna (blq) 212 km (132 mi), Roma Ciampino (cia) 221 km (138 mi) and Roma Fiumicino (fco) 234 km (145 mi).
Additional Services
Tours - The owner can schedule custom tours for your group. To learn about the tours available, speak to the owner when you arrive or inquire prior to booking. The cost will vary depending in the exact tour and number of people.
Villa Luana
Villa Oleandro
Pretty independent holiday villa with WIFI, private pool, TV, terrace, pets allowed, panoramic view
- 7
- 3
- 2
Description
Holiday rental Villa Oleandro is a lovely stone building that includes WiFi internet and private pool. The property can sleep up to seven guests comfortably in three bedrooms with two bathrooms. Conveniently located 6 km (4 mi) from Cortona, Italy and only 30 km (19 mi) from Montepulciano.
Your Experience
After arriving at Villa Oleandro you’ll find a beautiful clean well-maintained property with views of the hills ideal for a relaxing vacation in Tuscany. Regardless of how you spend your days - shopping, sightseeing, visiting museums or just driving in the countryside, when you arrive home you can relax with your family and friends at the pool for a perfect ending to another day in Tuscany. If you enjoy cooking for family and friends there is a well-equipped kitchen including coffee machine, microwave, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to seven people.
What's Nearby?
Most people enjoy visiting nearby cities and towns while on holiday, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Montepulciano 30 km (19 mi), Arezzo 33 km (21 mi), Perugia 49 km (30 mi), Assisi 66 km (41 mi) and Montalcino 66 km (41 mi).
Some other major tourist destinations you should consider visiting are: Florence 124 km (77 mi), Viareggio 217 km (135 mi), Forte Dei Marmi 224 km (139 mi), Rome 212 km (132 mi), Venice 373 km (232 mi) and Milan 417 km (259 mi).
Additional Information
Pets Welcome - If your pet is travelling with you on vacation that is not a problem at Villa Oleandro. If you have a large dog or multiple pets, please inquire for permission prior to booking.
Check-In Time: 16:00 - 20:00
Check-Out Time: 08:00 - 10:00
Pool Open: 15 May - 15 September (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 137 km (85 mi), Pisa (psa) 198 km (123 mi), Bologna (blq) 218 km (136 mi), Roma Ciampino (cia) 221 km (138 mi) and Roma Fiumicino (fco) 234 km (145 mi).
More Services
Professional Chef - Are you looking for a real treat during your vacation? Why not book a professional chef to prepare and serve you a delicious meal using local produce? The chef will arrange the meal based on your preferences and dietary needs. The chef will offer advice for the various courses and the wine. Ask for more details and the supplemental costs.
Tours - The owner can organize custom tours for your group. To learn about the tours available, speak to the owner when you arrive or ask prior to booking. The cost will vary depending in the individual tour and number of people.
Villa Oleandro
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- 6
- 5
Description
Villa Sole is a beautiful holiday rental (350 sq m) with WiFi internet, private pool and air conditioning. The property can sleep up to 11 guests comfortably in six bedrooms with five bathrooms. Villa Sole is located 6 km (4 mi) from Cortona, Italy and only 28 km (17 mi) from Arezzo in the tourist area "Cortona And Surroundings".
What to Expect
Upon arrival at Villa Sole you’ll find a beautiful clean well-maintained property perfect for a relaxing vacation in Tuscany. After a hectic day of shopping, spend some time with friends and family poolside enjoying a glass of wine - a perfect way to relax at the end the day. Sharing a meal with friends and family is a huge part of the Tuscan culture. Take advantage of the kitchen to prepare meals using local produce while on your holiday. The kitchen includes coffee machine, toaster, stove and refrigerator, as well as, plenty of tableware and cutlery for up to 11 people.
Visit the Area
Most people enjoy visiting nearby cities and towns while on vacation, so for your reference this is a list of popular places with distances (as the crow flies) from the property: Arezzo 28 km (17 mi), Montepulciano 33 km (21 mi), Perugia 54 km (34 mi), Montalcino 68 km (42 mi) and Assisi 75 km (47 mi).
If you'd like to visit the beautiful Tuscan coast, it's just a short driving distance to the sea from the vacation rental, only 15 km (9 mi).
Some other major tourist destinations you should consider visiting are: Florence 110 km (68 mi), Viareggio 194 km (121 mi), Forte Dei Marmi 204 km (127 mi), Rome 213 km (133 mi), Venice 353 km (219 mi) and Milan 397 km (246 mi).
Additional Information
Pool Open: 3 April - 30 October (If you'd like the pool open outside these dates, please make that request prior to booking)
Nearest Airports (distances as the crow flies): Firenze Peretola (flr) 118 km (73 mi), Pisa (psa) 178 km (111 mi), Bologna (blq) 202 km (126 mi), Roma Ciampino (cia) 222 km (138 mi) and Roma Fiumicino (fco) 235 km (146 mi).
More Services
Tours - The owner can organize custom tours for your group. To learn about the tours available, speak to the owner upon arrival or ask prior to booking. The cost will vary depending in the specific tour and number of people.
Villa Sole
